5,6,7,8-tetrahydro-2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazolo[1,5-a]pyridine | 203794-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6,7,8-tetrahydro-2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazolo[1,5-a]pyridine
• 英文别名: [(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-(5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl)oxolan-2-yl]methyl benzoate
• CAS: 203794-11-0
• 化学式: C₃₂H₂₉N₃O₇
• 分子量: 567.598
• InChiKey: FIFCMSZHTIFQIY-YULOIDQLSA-N

物化性质

• 沸点：
  749.384±70.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.372±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5,6,7,8-tetrahydro-2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazolo[1,5-a]pyridine 在 MaOMe 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (2R,3S,4R,5S)-2-Hydroxymethyl-5-(5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Synthesis and Antiviral Activity of 1,5-and 1,3-Dialkyl-1,2,4-triazoleC-Nucleosides Derived from 1-(Chloroalkyl)-1-aza-2-azoniaallene Salts

  摘要：

  Reactions of alpha,alpha'-dichloroazo compounds 2 with SbCl5 gave 1-(chloroalkyl)-1-aza-2-azoniaallene salts 3 as reactive intermediates. Cycloadditions of 3 with the ribofuranosyl cyanide 4 afforded the beta-D-ribofuranosyl-1,2,4-triazolium salts 5, which rearranged spontaneously to salts 6. Hydrolysis of 6 gave the 1,2,4-triazole C-nucleosides 7, which yielded the free nucleosides 8 after deblocking. Analogously, 12 was prepared from the cycloaddition of 4 with the alpha-chloroazo compound 10 in the presence of SbCl5. Deblocking of 12 with sodium methoxide afforded 13. Compounds 8a,b,e,f and 13 were tested against HIV-1, HIV-2, HSV-1 and HSV-2 and were found to be inactive.

  DOI：

  10.1080/07328319908044859
• 作为产物：
  描述：

  在 碳酸氢钠 作用下， 以 水 为溶剂， 以2.72 g的产率得到5,6,7,8-tetrahydro-2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazolo[1,5-a]pyridine
  参考文献：
  名称：

  Synthesis and Antiviral Activity of 1,5-and 1,3-Dialkyl-1,2,4-triazoleC-Nucleosides Derived from 1-(Chloroalkyl)-1-aza-2-azoniaallene Salts

  摘要：

  Reactions of alpha,alpha'-dichloroazo compounds 2 with SbCl5 gave 1-(chloroalkyl)-1-aza-2-azoniaallene salts 3 as reactive intermediates. Cycloadditions of 3 with the ribofuranosyl cyanide 4 afforded the beta-D-ribofuranosyl-1,2,4-triazolium salts 5, which rearranged spontaneously to salts 6. Hydrolysis of 6 gave the 1,2,4-triazole C-nucleosides 7, which yielded the free nucleosides 8 after deblocking. Analogously, 12 was prepared from the cycloaddition of 4 with the alpha-chloroazo compound 10 in the presence of SbCl5. Deblocking of 12 with sodium methoxide afforded 13. Compounds 8a,b,e,f and 13 were tested against HIV-1, HIV-2, HSV-1 and HSV-2 and were found to be inactive.

  DOI：

  10.1080/07328319908044859

文献信息

• Al-Masoudi, Najim; Hassan, Nasser A.; Al-Soud, Yaseen A., Journal of the Chemical Society. Perkin transactions I, 1998, # 5, p. 947 - 953
  作者：Al-Masoudi, Najim、Hassan, Nasser A.、Al-Soud, Yaseen A.、Schmidt, Patrick、Gaafar, Alaa El-Din M.、Weng, Min、Marino, Stefano、Schoch, Annette、Amer, Atef、Jochims, Johannes C.

  DOI：——

  日期：——